Benzyl 3-[N-(1-(S)-ethoxycarbonyl-3-phenylpropyl)-L-alanyl]-2,3-dihydro-5-phenyl-1,3,4-thiadiazole-2-(S)-carboxylate → 3-[N-(1-(S)-Ethoxycarbonyl-3-phenylpropyl)-L-alanyl]-2,3-dihydro-5-phenyl-1,3,4-thiadiazole-2-(S)-carboxylic acid

HRID 1651441Notes

Reaction equation

HRID 1651441 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]([NH:15][C@H:16]([C:18]([N:20]1[N:24]=[C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[S:22][C@H:21]1[C:31]([O:33]CC1C=CC=CC=1)=[O:32])=[O:19])[CH3:17])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:5])[CH3:2]>C(O)C.[Pd]>[CH2:1]([O:3][C:4]([C@@H:6]([NH:15][C@H:16]([C:18]([N:20]1[N:24]=[C:23]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[S:22][C@H:21]1[C:31]([OH:33])=[O:32])=[O:19])[CH3:17])[CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 13773252Benzyl 3-[N-(1-(S)-ethoxycarbonyl-3-phenylpropyl)-L-alanyl]-2,3-dihydro-5-phenyl-1,3,4-thiadiazole-2-(S)-carboxylate

Product 1

HCID 137732543-[N-(1-(S)-Ethoxycarbonyl-3-phenylpropyl)-L-alanyl]-2,3-dihydro-5-phenyl-1,3,4-thiadiazole-2-(S)-carboxylic acidYield 36.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of the product from step (c) (0.26g) in ethanol (20ml) was treated with 10% palladium on charcoal (0.lg) and stirred in a pressure vessel under hydrogen at 3 atmospheres at room temperature for 3 days. The catalyst was filtered off and the filtrate evaporated. The residue was triturated with ether to give the title product (0.08g) as a white solid, m.p. 180.5°-182°.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate evaporated
  3. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-097d39793d72444bbdd2144d6138e646
Source dataset
uspto-grants-1990_05
Patent number
US04927822

Reaction notes

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